amitriptyline   

GtoPdb Ligand ID: 200

Synonyms: amitryptiline | Elavil® | Endep®
amitriptyline is an approved drug (FDA (1961))
Compound class: Synthetic organic
Comment: Amitriptyline is a tricyclic antidepressant (TCA).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: amitriptyline

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 3.24
Molecular weight 277.18
XLogP 4.93
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CN(CCC=C1c2ccccc2CCc2c1cccc2)C
Isomeric SMILES CN(CCC=C1c2ccccc2CCc2c1cccc2)C
InChI InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
InChI Key KRMDCWKBEZIMAB-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1961))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
dimethyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene]propyl})amine
International Nonproprietary Names
INN number INN
976 amitriptyline
Synonyms
amitryptiline | Elavil® | Endep®
Database Links
BindingDB Ligand 50020712
CAS Registry No. 50-48-6
ChEBI CHEBI:2666
ChEMBL Ligand CHEMBL629
DrugBank Ligand DB00321
DrugCentral Ligand 180
GtoPdb PubChem SID 135649939
PubChem CID 2160
RCSB PDB Ligand TP0
Search Google for chemical match using the InChIKey KRMDCWKBEZIMAB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KRMDCWKBEZIMAB
Search PubMed clinical trials amitriptyline
Search PubMed titles amitriptyline
Search PubMed titles/abstracts amitriptyline
Search UniChem for chemical match using the InChIKey KRMDCWKBEZIMAB-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone KRMDCWKBEZIMAB
Wikipedia Amitriptyline